Top 5 Blunders to Avoid When Changing Careers, with Kathy Caprino

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Transcript

Mac Prichard:

Hi, this is Mac from Mac’s List. Before we start the show, I wanted to let you know about my new book, Land Your Dream Job Anywhere. I’ve been helping job seekers find meaningful, well-paying work since 2001, and now I’ve put all my best advice into one easy-to-use guide.

My book shows you how to make your resume stand out in a stack of applications, where you can find the hidden jobs that never get posted, and what you need to do to ace your next job interview. Get the first chapter now for free. Visit MacsList.org/anywhere.

This is Find Your Dream Job, the podcast that helps you get hired, have the career you want, and make a difference in life. I’m Mac Prichard, your host and publisher of Mac’s List.

I’m joined by my co-hosts, Ben Forstag, Becky Thomas, and Jessica Black from the Mac’s List team.

This week we’re talking about top blunders to avoid when changing careers.

Many of us will change careers several times. Doing this, however, isn’t easy. In fact, too many workers stay in jobs they don’t like. Or they make a change and discover it isn’t what they expected. Our guest expert this week is Kathy Caprino. She says people who struggle with switching careers make five or more blunders. We talk about these mistakes and how to avoid them later in the show.

The first step in switching careers is knowing what you want to do next. Ben has found a website you can use to find careers and it’s based on your personal and professional interests. He tells us more in moment.

You want to move across the country to a new city. How do you get your resume noticed without making a connection in person? That’s our question of the week. It comes from Seth Richardson in New York City. Becky shares her advice shortly.

As always, let’s check in with the Mac’s List team.

Our topic this week is The Top Blunders People Make When Switching Careers. Kathy’s got a list of five and she has some others, I’m sure that she’ll want to talk about. These are common mistakes that either keep us from changing sectors, or maybe we were doing it in a way that’s more painful than it needs to be.

I think everyone around the table struggled with switching careers or sectors, and I’m curious, what have been some of your biggest challenges when you’ve done that?

Ben Forstag:

I’ll start. So I think the biggest problem for me is there comes a time in every career or job trajectory where you realize you don’t want to be doing that anymore but the challenge I’ve had is not knowing exactly what I want to do. Knowing that I want to do something different, but not knowing what exactly that is.

Jessica Black:

That was my struggle too.

Ben Forstag:

Yeah, so it’s getting down to having a clear goal of what you want to be doing because it’s really hard to sell yourself to another employer or to transition to a new industry when you don’t really have a clear idea of where you’re trying to go.

Jessica Black:

Yeah I agree. I had a lot of that struggle, especially early on in my career. So I’ve talked a little bit about this before, but I did a lot of different jobs, and that was great because I just wanted to try a bunch of things and see what worked and where I had some strengths. It kind of helped me get clear on my goals. Which, it’s really the long way to go; it took awhile, but that was really the only way for me to do it. I have to be able to do it by doing it.

Mac Prichard:

Yeah, you’re almost an experiential learner aren’t you, Jessica?

Jessica Black:

Yes. I am. Plus I just like to gain that experience and I like to do it all as you guys probably know. I want to do it all so I just continued to gain the knowledge and all of that. But over the course of my early career history, I learned what worked and what didn’t and what I wanted to keep pursuing and maybe what I didn’t want to pursue. Even though I enjoyed the things that I did, I found out that there were things that I wasn’t gravitating towards as much and those types of things. Fundraising being one of them. So lots of things like that, that helped me figure out where I was getting my energy and where my strengths and my skills lay. But yeah, that was helpful.

Becky Thomas:

I feel like I don’t think those are blunders though. It’s like you have to go through that stuff to know what you’re good at and what you’re not good at. What you enjoy and what you don’t enjoy. I sort of had the same thought when we were talking about this, but blunder…I don’t know if it’s an error necessarily.

Jessica Black:

No, you’re right.

Becky Thomas:

I think that it does take time but you also have to just go through stuff, especially when you’re changing careers. It’s not just going to go overnight.

Jessica Black:

Absolutely.

Becky Thomas:

You have to do it in stages.

Ben Forstag:

Yeah, I think it’s a really normal thing and I’m guessing most people go through it. I think the blunder is thinking that you can force your way through it anyway. That you can make other people believe that you’re really passionate about it when you haven’t really figured it out on your own side.

Becky Thomas:

That’s true. Right.

Jessica Black:

Fake it till you make it.

Becky Thomas:

Yeah, that’s a good point. I think there’s a fine line there, but you do have to figure out what you want to be doing, but know that it takes time and effort to get there.

Jessica Black:

Yeah, and I guess I’ll say maybe more along the lines of what you’re trying to say of, the blunders side of things, is when…and I was still in my process of trying to figure it all out, but, I don’t know, I’ve talked about this before as well, I’m an eternal optimist. So I would always think, there would be times when I would think, “Oh no, I’ve figured it out. I want to do this now, and this is what I want to do and it’s all going to work out. Here’s my plan.” And then thinking that it would be an easy switch to make that transition when I didn’t have concrete experience in that other thing that I thought I wanted to do.

Then just going in and being like, “Hey, I’m great at this, and I can do it.” And kind of being that young person that thinks they have the world at their feet, I guess. That all the doors are open and you can just go in and have enthusiasm and you can just make it happen if you just try hard enough and that doesn’t work. Sometimes it does but that’s not the only thing that works so you do have to make those connections and you do have to put in the work and show that you are capable of making it happen. So there were definitely times when I had some dreams dashed, thinking that I was just going to waltz in and have everything solved for me. But that was a big learning process too, because eventually I learned that those jobs that I had in my head that I was wanting, weren’t actually what I was wanting. But you know, it’s one of those.

Mac Prichard:

Well I think that a lot of people learn by doing, just as you do, Jessica. I think it’s a very common learning style and I think also, to Becky’s point, when Ben and you and talked about the challenges of figuring out what you want to do, that’s a common problem that we all face. And I know when Kathy is thinking about blunders in switching careers or sectors, she’s got some very specific things in mind and we’re going to dig into those.

Jessica Black:

Yeah, that’ll be good to hear.

Mac Prichard:

Yeah. I will say, that in my case, I’ve shared the same challenge that you and Ben mentioned, which is figuring out what to do next. I’ve gotten stuck several times trying to do that, and there are ways, and we’ve talked a lot about this on the show, about how to get clear about your goals and informational interviews, networking, and self-assessment are part of that.

The other thing that surprised me when I switched from the nonprofit to the private sector, was just adjusting to the culture of working inside a large corporation. I wasn’t prepared for that, and I would encourage people to consider that before making that leap.

Jessica Black:

It’s a big change. Yeah, good.

Mac Prichard:

Well terrific. Well let’s turn to you Ben, because you’re out there every week exploring the internet on behalf of our listeners, looking for those tools, books, and websites that people can use in their job search and careers. So what have you found for us this week?

Ben Forstag:

So this week I’ve got a resource to help folks who are having that problem that Jessica and I talked about of not really knowing what you want to do next. Again, we all get stuck in “I’ve always been an accountant.” Or, “I’ve been in law for the last twenty years.” And they can’t think beyond what they’ve been doing, even if they’re unhappy in it.

Jessica Black:

If you don’t mind if I interrupt? The flip side that I had was too many interests.

Ben Forstag:

Yeah, I guess that’s a being spoil by abundance. That’s a good thing to have, but it’s really hard taking all of those interests and focus them down.

Jessica Black:

Right. Sorry to interrupt.

Ben Forstag:

Oh no, it’s okay. Thank you.

So I found this resource online, it’s called the Career Cluster Interest Survey, and it comes from the Minnesota state university system in their Career Wise program. Now I’m guessing this is something they developed for their own students but it is open to the public, and the url we’ll have in the shownotes, because it’s one of these really long urls.

But the way this works is, everyone has a different way to describe themselves and what they like to do, and their interests and their goals and things like that. So everyone has a different way to describe themselves and what they like to do. This survey lets you rate the activities you enjoy and your personal qualities, even subjects that you enjoyed in school, and then you can see what career clusters are matched for your interests. It’s a list of one hundred and fifty-two yes or no questions about specific interests, activities, personal education, things like that.

That’s a lot of questions but it only takes about ten minutes because all you’re doing is checking off boxes for traits that relate to you. And at the end of the survey you see a list of career clusters that are a good match for your interests. Now one of the reasons that I really liked this tool was because it gives you a cluster of careers. It’s not like a straight line saying, “You must be a graphic designer.” Or, “You will be a symphony composer.” Those can be really narrow and sometimes they completely miss the mark. What you get in this survey is a cluster of six or seven general careers that might suit your temperament, and then from there you can drill down into specific careers within that cluster of things you might want to think about.

I think this is just a nice way to start that winnowing process of whether you don’t know where you want to start, or you want to move to, or if you have too many interests like Jessica here, and you need to just winnow that down. I think this is a really nice tool for doing that. So again, it’s the Career Cluster Career Interest Survey, and that’s a mouthful. We’ll have the url in the shownotes.

Mac Prichard:

So I’ve got to ask a question that I suspect is on the minds of some of our listeners, Ben. What did you learn about yourself in answering the one hundred and fifty-two questions?

Jessica Black:

You’re supposed to be a managing director.

Ben Forstag:

I’m supposed to be a graphic designer or lead a symphony. No.

I think it kind of pegged me right. I mean, I don’t know many people who close their eyes and dream of a management job. But I’m happy with my job and it said, “This a career area you might want to investigate.” There is some flexibility here because it’s also asking about personal interests outside of the professional space because those two fields of your life definitely overlap. So sports agent was one of the careers that came up there.

Jessica Black:

Nice.

Mac Prichard:

I could see that.

Jessica Black:

Yeah.

Mac Prichard:

You’re a big sports fan.

Jessica Black:

The Cleveland Indians.

Mac Prichard:

Yeah.

Ben Forstag:

Yeah. Or like law, which I broke my grandmother’s heart by not becoming a lawyer. So it gives you a nice, wide array of things and I guess I could see myself in the careers, but I’m pretty happy where I am right now.

Mac Prichard:

Okay.

Jessica Black:

That’s awesome. It sounds like a really cool tool. I’m definitely going to use it.

Mac Prichard:

Great. Well I will check that out too, and I’m sort of reminded of the latest season of The Unbreakable Kimmy Schmidt on Netflix. She took an assessment like this.

Jessica Black:

Oh yeah.

Becky Thomas:

That’s on Crossing Guard. I love that show.

Jessica Black:

It’s so good.

Becky Thomas:

The Crossing Guard test that she does. She like takes the truck and she’s like, “Come on in.” And she dies, and they’re like “You win.” That was so good. Oh, that was probably a spoiler.

Jessica Black:

I think people were waiting with bated breath to watch it. Which everyone should watch, it’s so good.

Becky Thomas:

Yeah, it’s been out for months. The Unbreakable Kimmy Schmidt.

Mac Prichard:

Yeah, it’s a good show, and tools like this are really useful to have because people do get stuck, as you said, Jessica, figuring out exactly what to do next, or to sort out among competing interests.

Jessica Black:

Yeah.

Ben Forstag:

I would just throw in there that, and I think most people know this, in your heart you’ve got a gut feeling about what feels right and what doesn’t, about what you want to be doing. So I don’t know anyone who’d take one of these tests and the answer comes out and it just feels completely wrong and they run with it anyway. That’s as bad as listening to your grandmother and going off and getting a law degree that you didn’t want. So I think this is just a good way to reaffirm things that might be in the back of your mind, even if they’re not conscious thoughts.

Jessica Black:

Well, I will also, in response to that, I think that is absolutely true, but if you are sort of on the fence and you’re not decisive enough to decide which traits you feel are accurate for you, it can come out skewed. If you give a wide variety of personal interests or whatever, it may not be able to be honed in. So be very honest and do a little bit of self-assessment beforehand and be in the right mindset to do it. Because in college I took a Myer’s Briggs personality quiz my freshman year of college, and it came out completely different than what I actually am, because I wasn’t clear about who I was. So I was answering things that I thought that I should answer rather than what I actually was. So not that I made any decisions based on that personality test, but it definitely, now that I know myself a lot better, it’s interesting to have that realization. Anyway, that’s a long story.

Becky Thomas:

That’s a good point.

Jessica Black:

Yeah.

Mac Prichard:

Alright, well thank you for that, Jessica.

Let’s turn to you, our listeners, because Becky is here to answer one of your questions. So Becky, what’s in the mailbag this week?

Becky Thomas:

So this week’s listener question comes from Seth Richardson, from New York City.

“Hi, this is Seth from New York City. I am in the process of relocating to Portland. Can you give me some advice on how to get my resume noticed from across the country when I can’t always be there in person to make the face-to-face connection?”

So this is actually interesting because I met Seth in person. He was in the building meeting with career coach and friend of the podcast, Aubrey Declerck, and she was helping him get connected and meet with folks who are in town. He was doing a little informational interview tour/spree, as he was getting ready to move here. I think he was moving in the fall, and so he was really just trying to get his network built and came in and we were chatting a little bit. And I was like, “You have a listener question, let’s record it real quick.” So he was really sweet and great and we’ve connected since then. So thanks again, Seth, for doing that for me.

We chatted about this a little bit, but I hear this from a lot of other people too. Just, “I’m trying to move to this city. I’m really excited about living there, but I want to try to get connected and hopefully get a job before I move.” So I had some tips for Seth that I wanted to share with everyone else too.

So he asked specifically about resume; how do you get your resume to stand out? And I think that there’s a couple of tactical things that you can do, and one of them was removing your current address from your resume. You don’t have to list that anymore. I feel like it’s not really super relevant for employers. When I first was trying to move to Portland and getting a job, I actually put my friend’s Portland address down just to be like, “I’m in Portland, yeah. Totally.” I was definitely planning to move so it wasn’t too…

Jessica Black:

Yeah, no that used to be a pretty common practice too. That’s fine.

Becky Thomas:

So that’s something you can think about, and you could even just put the city that you’re looking to move to, and have a plan to move there. Just to say that you’re in that city or you will be soon.

Also, when you’re applying for jobs, try to be as open and honest about your story as you can. Really try to draw that employer in with the story of your excitement and your passion for this new city that you’re moving to. How you’re already plugged into that city and you’re moving at this date, you’ll be there, you’ll be ready to work at this date, and you’re totally fully excited about this position in the city. Don’t try to hide it because I think that if you are planning to move and you’ve got that date down, there’s no reason to, and I think you can sort of use that to your advantage. That you’re fresh into the city and you’re excited and you’re totally ready to jump in with both feet.

Jessica Black:

Yeah, and they’ll find out anyway, so you might as well just be up front about it. I like that.

Becky Thomas:

Yeah, Use it as a tool.

Mac Prichard:

Yeah, I like it too, because if you don’t address why you’re moving and when, people will assume you’re fishing.

Becky Thomas:

Yeah they’ll fill in the blank with weird stuff. So own that story and make it as compelling as you can, because it is exciting. You’re in this new phase and they can be a part of that, and you’ve got a lot of energy and all that stuff. That’s true for Seth.

Then there’s a lot of other things you can do besides just trying to make your resume stand out. Starting to network is a huge thing. In most cities, you have to build a network to get into whatever industry you’re in. So use people you already know to get introduced to new folks. It’s really helpful to make a short list of companies you want to target, and use anyone you’re connected to to see if they know anybody and try to get some more formal informational interviews scheduled. Then if you can, go visit that city, and schedule some of those informational interviews for in person. And also try to attend as many networking events as you can within the days that you’re going to be there. Just really get in front of the people in the city that already are connected and have great jobs, and they’re going to be able to help you out a lot.

So sometimes it’s a matter of just moving and you’re going to have to network your way into a job within a couple of months of moving, and just take that risk. Because it can be scary, but I think it is a challenge before you move to land that job, but there are a lot of things that you can do. So try all of those things, do your due diligence, and if worse comes to worst, move here and hustle your way into a job as soon as you can. Yeah that’s as far as I can go with my advice. Anything I’m missing here guys?

Jessica Black:

That’s great.

Ben Forstag:

I’d also add that it behoves you to really explain how you could interview for the job remotely. Don’t leave it up to the hiring manager to figure that out. Be real up front in your application or your cover letter, saying, “I’m in New York City, I know you’re in Portland. I’m happy to do a Skype interview, or I could do a phone interview.If we feel like it’s a good fit after that, I’m happy to fly out for an interview.” and I know some people worry about, “Who’s going to pay for that flight out?” I would say, just try to put all the barriers out of the way so you can have that conversation and it may well be that after the first Skype call you’re not interested in the job anyway.

Jessica Black:

But showing your willingness is what you’re saying and I think that’s really important.

Ben Forstag:

Yeah. Just show the roadmap of how you two could get to know each other might look.

Becky Thomas:

Yeah because the hiring manager is stressed and busy, and if you sort of lay it out for them, they’ll be like, “Oh hey, this person’s thought it  through, they’re going to take care of me, this is going to be an easy process I might as well get in touch with them and talk to them.”

Jessica Black:

“And they’re serious about the job.”

Becky Thomas:

Yeah, totally.

Mac Prichard:

Yeah, and I love your idea about making a job hunting trip. Because when you set those dates, and if you can spend a week, I encourage you to do that because then you can go back to places where you are a candidate and say, “I will be in your town on these dates, and I would love to sit down with you while I’m there in person.” And that may pull your resume out of the pile and get people, if not to give you a formal job interview, at least to sit down with you informally. It also gives you a great reason to reach out to people that you want informational interviews with to have face to face conversations.

Jessica Black:

Yeah, and building those connections that’s good.

Mac Prichard:

Well terrific, well thank you. Thank you, Becky and thank you, Seth.

f you’ve got a question for Becky, please send her an email. Her email address is, becky@macslist.org. You can also call our listener line. That number is area-code,  716-JOB-TALK – Or send us a tweet, and our Twitter handle is, @macs_list

If we use your question on the show, we’ll send you a copy of our new book,  Land Your Dream Job Anywhere.

We’ll be back in just a moment. When we return, I’ll talk with this week’s guest expert, Kathy Caprino about top blunders to avoid when you change careers.

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Now let’s turn to this week’s guest expert, Kathy Caprino.

Kathy Caprino is a career and personal success coach, a writer, a speaker, and a leadership developer dedicated to the advancement of women worldwide.

She is also the author of Breakdown, Breakthrough, and the Founder of Ellia Communications, Inc. and the Amazing Career Project.  And Kathy is a contributor to ForbesHuffington Post and LinkedIn.

She joins us today from Stamford, Connecticut.

Kathy, thanks for being on the show.

Kathy Caprino:

Thanks so much for having me, Mac.

Mac Prichard:

It’s a pleasure to have you.

Now our topic this week is blunders and mistakes people make when switching careers and we hear on our show Kathy, and I know you do in your practise, from so many people who want to change careers or sectors. Why can it be difficult for people to make this change?

Kathy Caprino:

Well, I speak from experience because I tried to do it after an eighteen year corporate career and I bombed out, and thankfully I’ve learned how to do it. But the problem is the following; first of all, many of us just land in an area of work or field without really conscious, deliberate intent and then we spend a few years and we’re trying to be successful and do well and get promoted. And so many people then wake up, often in midlife and say, “What am I doing? I have achieved the success, I wanted but I’m miserable.”

And I think that’s the world I work with and when you’ve gotten that far along the path, it’s number one, very scary to change because you feel like you’re going to give up everything. Secondly, what I hear more than anything else, “I know what I don’t want, but I don’t know what I do want.” So it’s confusing, it’s hard, and we’re not really trained to navigate these challenges very well, Mac, I find. Do you find that too?

Mac Prichard:

I do. I have heard from so many people who describe exactly the experience that you just outlined which is, starting a career wanting to get going and picking a job. It’s something that interests them, but the years go by and suddenly it’s ten or fifteen years later, and as you say they’re not happy, they’re ready for a change. But they get stuck about what to do next.

Kathy Caprino:

That’s it.

Mac Prichard:

Yeah. So Kathy, how do you see people get unstuck? What typically is the first step someone might take?

Kathy Caprino:

Well actually, Mac, I’ve developed, after doing a lot of research and interviewing a hundred women who’ve overcome professional crisis… I do have a five step model and I’ll just share it with you very quickly.

It’s number one, step back for an empowered perspective of who you are. So often when you’re in a challenging situation or toxic boss or you’ve been laid off, you’ve lost the connection to how great you are. I really believe that everybody on this planet is brilliant and amazing in their own way. So you have to take a step back and look at who you’ve been over your lifetime, not just the tip of your nose.

The second step is to let go of the thinking patterns and behaviors that keep you stuck. That’s the most important. You know, I’m now a trained therapist after years in corporate, and I use that therapeutic lens in coaching. So many of us engage in habits and patterns that are sabotaging but we don’t know that we’re doing it. So we do have to let go of those patterns before we can have a better career and a better life experience.

The third is to say yes to your compelling visions. So many people, they might fantasize, “Let me run a bed and breakfast, or maybe be a best selling author”, but in terms of really doable steps, they’re at a loss. But first we have to say yes to what those compelling visions in our life are.

The fourth step is to try it on. This is another thing we just aren’t taught to do. So many people will project onto something, like, “Oh I want to work in a non profit,” or, “Oh, Academia will be great.” Well I have a lot of clients who want to run from both of those scenarios. Not all nonprofits are created the same. We have to try on, physically, behaviorally, emotionally, financially, spiritually, the directions we’re contemplating. And often we’ll find out that the fantasy isn’t going to make us happy.

Then the fifth step is to create it smart. This takes time and so many people have lost patience; they’re in a toxic situation, they want out, they feel unhappy, and they want to jump but this is a process that takes time. So you want to create it with a plan and an accountability buddy if we can.

Mac Prichard:

I love the fact that you’ve laid out five concrete steps that people can take positive action to move forward and that we started with that. Because our topic this week are the pitfalls that people need to avoid. The blunders, and we do this is a constructive way because we want people to find that next career or switch into that new sector with as little pain as possible and to do it as quickly as they can. So let’s talk about these blunders, Kathy, these pitfalls that you see people need to avoid. What’s the top one? What’s number one on your list?

Kathy Caprino:

So the top one is something I’ve coined “the pendulum effect.” And here’s what it is: for many people, they’ve waited too long in something that makes them unhappy, and that unhappiness can be on a spectrum from miserable and facing discrimination and harassment like I did in my last job, or just feeling like, “I’m in the wrong thing.” But what happens is, when we wait too long, then there’s pain and then we want to run away.

So many people do what I did which is, after I got laid off after 9/11, it was so brutal that I said, “I don’t ever want to see the inside of a corporate office again. I never want to put on a suit. I’m done.” And I became a therapist. And that in and of itself wasn’t a mistake but the pendulum piece was, “Oh, I’m going to run to the opposite ends of the earth, from corporate to therapy because that will heal all of my problems.” What happens is, only you can heal your problems. The new job, the new industry, the new direction, isn’t going to necessarily heal it all. So we want to run into something that’s very different, away to something that’s very different, but what we’ll find is if we haven’t addressed some of our core issues, it’s going to repeat in this new job, in this new career.

And some of those core issues are how you communicate, the level of emotionality you have, the toxicity that you’re used to, that you can actually attract because you’re boundaries aren’t strong, how defensive you are, how not good at constructive criticism, how alone you are if you don’t have a support network, how your leadership skills are, and all of that. So we’ve got to address that before running away.

Mac Prichard:

So understand what’s making you unhappy or what’s holding you back so that you can address those problems and also that will make you an even better candidate and more successful in whatever it is you choose to do next.

Kathy Caprino:

Absolutely. I mean I call it, you’re a better energetic match for a very positive future, than if you just run away. Because then you haven’t done the work and you’re going to attract more of what’s made you unhappy.

Mac Prichard:

Okay, so avoid the pendulum effect. What’s another pitfall you see people get trapped in?

Kathy Caprino:

Yes, so I think the reason so many mid-career people stay stuck is when they’re trying to think about what they want, they, I call it, “Glomming onto the wrong form of work”. Let me give you a perfect example- I have a lot of corporate people say to me, “I’m so done with this nonsense, these politics, and this toxic, narcissistic boss. I want to start my own business.” Well Mac, as you know, because you run a number of thriving businesses, running away is not a reason to start a business.

So many people are also risk-averse; it keeps them up every night, all night. The entrepreneurial spirit, it’s too scary. So you have to understand who you really are, and look at the essence of what you want and then find the right form of it.

So that means, look at your true talents that you love to use, not the skills you hate to use. A lot of us are very skilled at things that we actually hate doing. We want to look at those natural talents that make us happy, we want to look at the outcomes that make us feel alive, positive, a positive contributor in the world. We want to look at the environment that we want. I always struggled in the corporate world, I just found it so restrictive. I’m so much happier out on my own in my own business. We want to look at our standards of integrity. We also want to look at the financial compensation that we need. And frankly a lot of people will say, “I need two hundred thousand,” when in fact, it’s a lot less than that but they’re just used to that. They think they have to replicate it.

But we have to look at also the flexibility that we want, the balance that we want in our life. Once we get really clear on that, then we’re going to find the right form of it. But we just don’t want to assume, “Eh, I want to be a consultant, or an entrepreneur”, when we really don’t know what it is we want to create.

Mac Prichard:

And another version of this, and I think you touched on this a moment ago, Kathy, is the fantasy job. I lived in Boston for nine years, and New England was full of beds and breakfasts that were started by people who were fleeing New York City, or Washington DC. The reality of serving meals, cleaning toilets, and washing bedding everyday is very different than actually being a guest at one of those places. And many people struggle with that and often quit as you know.

Kathy Caprino:

You know Mac, that’s funny, so many people…I have something called a Career Path Assessment, a set of questions I think everybody should answer before they make a change. So many people say, “I want to launch a bed and breakfast.” And I’ve had a number of clients go and try that on. “I want you to go to five different bed and breakfasts, interview the owner, what it’s like.” And they all, everyone one of them, came back and said, “I don’t want to do that, but what I do want to do is create events, or design, blah blah blah.” So they learn from that try on process. But I had no idea so many people wanted to start a bed and breakfast.

Mac Prichard:

Yeah, I think it looks glamorous from the outside maybe. But I love the fact that you’re having people go out and try the job on for size and that gets back to your earlier point about being clear about what it is you want and what’s involved in a job. Other blunders, Kathy, that people should know about so that they don’t make those same mistakes?

Kathy Caprino:

I’m going to offer you the third that I think is so important. I think in general we are not raised to know ourselves. I think in our society there’s so much pressure; pressure to achieve, pressure to live up to and exceed other people’s expectations. We don’t really know who we are and we certainly aren’t encouraged to resist what our tribe wants for us. I think you probably know what I mean.

In order to be happy, in order to build a career you’re so proud of, you have to honor who you innately are. There are ways to do it; look at who you were as a teen. I mean when I look back as an eighteen year old, it’s everything I am today. I just didn’t recognize, how much these…you know I’m a writer, a speaker, I’m a singer, I love to be on stage. Young people would come and ask me questions about their life, and I would say to my mom, “I’m eighteen. Why are they asking me these life questions?” I think I had kind of a therapeutic ear even back then. So who are you? What lights you up? What have you always been? What agitates you? What are your true passions? What is the legacy that you want to leave behind? You can’t have a great career if you don’t know the answers to these questions.

And it really comes down to, honor who you are. Make yourself right, not wrong, and pursue what you’re most passionate about.

Mac Prichard:

What about finances, Kathy? You touched on this a moment ago when you were talking about expectations for salary, and understanding too, that maybe you don’t need as much. To earn as much as you have in the past. How important are finances in switching careers?

Kathy Caprino:

Well, they’re critical. When I first started coaching eleven years ago I was much more free to say, “Hey, let’s go pursue your passion; dwhat you love, and the money will follow.” Well that’s not necessarily true. You’ve got to do it in the right way for money to follow. You have to be incredibly savvy today. For instance, if anyone wants to be a coach, my gosh, you are an entrepreneur, you are a business person, and it also involves online marketing and communication, and social media. So you must do it in the right way.

Another thing I tell people…and I can’t tell you how many people say, “I want to write a bestselling book” and they fantasize that they’ll be able to leave everything behind and simply write on the beach, you know? Tulum, Mexico. Most writers, most best selling writers I know don’t do it for the money, and they do many other things. So we can’t let our fantasies shape what we’re actually doing here. If you really want to start your own thing, or you really want to be an author, or be a creative, or be a jazz musician, I think one thing you’ve got to realize is that your art has to be of service to the world. It can’t just be because “I like to write poems.” Is your poetry of service? Is it helping people?

So if you really want to do something different, you need a transition plan. It’s not going to happen overnight. I say to a lot of new coaches…I train coaches now…most coaches don’t make more than twenty thousand the first year and many of them go broke. You’ve got to know what’s involved and then build a transition plan including how you’re going to fund this change. And when you do it right, then the finances will work for you and with you, not against you.

Mac Prichard:

I love that you’re pointing out the value of talking to people who are already doing something and learning from their experience, and recognizing that that first, or second, or third year when you’re launching a consulting practise or going on the path of self-employment or opening a business, it’s probably going to be a lean year or two, and you’ve got a plan for that.

Kathy Caprino:

A hundred percent. And I have a quick anecdote. When I was first thinking of being a therapist, I did interview a few people, but you know who I chose? Really wealthy therapists who were making over a hundred thousand, who were writing best selling books, and didn’t need insurance. Well awesome, but that’s only one part of the spectrum. I should have interviewed twenty other people working in social service agencies, not making a lot of money or people who left the field. Don’t let your research just be a self-fulfilling prophecy that I’m going to be a millionaire. Make sure you’re interviewing a wide spectrum of people and you’re looking at it with your eyes wide open.

Mac Prichard:

And finally, I know another blunder that you’ve written about on your blog is the timetable. Just having realistic expectations about the amount of time it takes to make these changes. Tell us more about that, Kathy.

Kathy Caprino:

Yeah, you know, another blunder I see, and a lot of this is coming from my Forbes post, that has five hundred and seventy-one thousand views and growing, people give up too quickly. You know, I was talking to a Tony Robbins coach years ago and he said, “I don’t care what my clients want.” I said, “You don’t? What do you care about?” He said, “What they’ll commit to. What they’ll give up everything for.”

So many people start on a direction and if it doesn’t pan out in six weeks, six months, even people on social media, they’ll try this, and if in two months they’re not generating revenue from it, they give up. That’s not going to work, you’re going to fail. You’ve got to choose a direction that has so much juice for you that you will stay in it and give up everything for it really. Or at least give it a sufficient amount of time, a few years let’s say, given what direction you’re talking about. Where you’re willing to go through the bumpy road because it is bumpy. Isn’t it, Mac? Change is bumpy. It’s not all a walk in the park.

Mac Prichard:

Yeah, I know I’ve talked on this show before; I can describe my career in a way that makes it sound glamorous and unrelentlessly successful, and you think it’s a forty-five degree angle, but every career has it’s ups and downs. There’s always going to be valleys as well as peaks.

Kathy Caprino:

That’s it.

Mac Prichard:

Yeah.

Kathy Caprino:

And you’ve got to have the perseverance to stick through it until you get to your goal.

Mac Prichard:

Great advice, Kathy. Now tell us, what’s coming up next for you?

Kathy Caprino:

Oh yeah. One thing I just love to talk about is I do have a course. It’s a career transformation course, but really, people change personally as well in every way and it’s called The Amazing Career Project. I launch that every fall and every spring, so we do have a launch coming up. It’s amazing, and it’s an online course. It’s a wonderful group component, where people are helping each other online and on Facebook. It’s sixteen weeks with sixteen videos and homework assignments. So that’s at theamazingcareerproject.com. And anyone who loves group support, who wants a nice process that’s going to get them to their goal, I hope they’ll check it out.

Mac Prichard:

Terrific. We’ll be sure to include a link to that in the shownotes.

Kathy Caprino:

Thanks.

Mac Prichard:

It’s our pleasure. And Kathy, I know people can also find you on your website, which is, kathycaprino.com.

Kathy Caprino:

That’s it.

Mac Prichard:

Alright. Well Kathy, thanks for joining us this week.

Kathy Caprino:

Thank you for having me, Mac. Great to talk to you.

Mac Prichard:

You, too. Take care.

We’re back in the Mac’s List studio, with Becky, Jessica, and Ben. I enjoyed that conversation a lot. Thank you, Kathy.

Jessica Black:

That was great.

Mac Prichard:

Yeah it was. What are some key points you all heard Kathy make? Ben, it looks like you want to go first. You cutting in front of Becky here?

Ben Forstag:

Don’t start a bed and breakfast.

Jessica Black:

Yeah.

Becky Thomas:

Oh come on, I want to.

Jessica Black:

“It looks so quaint and lovely.”

Becky Thomas:

I love breakfast. I love having a garden and cutting flowers and fresh linen.

Jessica Black:

Then maybe it is perfect for you. Maybe you’re the key demographic for the starting a bed and breakfast.

Ben Forstag:

I think that’s the customer demographic, not the owner demographic.

Becky Thomas:

I know. It’s like having a customer’s perspective, “This is wonderful.”

Jessica Black:

But that’s where if you have…if you like cutting flowers and somebody else likes doing laundry, you just have to find that person who does the things that you don’t like to do.

Becky Thomas:

Yeah, for sure.

Jessica Black:

And then make a partnership and it might work out.

Becky Thomas:

Yes. that’s what Kathy was saying about keeping your eyes open, right?

Jessica Black:

Maybe that’s what she meant. We can interpret it that way.

Ben Forstag:

Seriously, though. The piece of advice that she offered that I liked the most was watching out for the pendulum effect of running away.

Jessica Black:

Yeah, that was huge. Yeah.

Ben Forstag:

To the complete opposite of what you’re doing now. I think everyone’s done that in one way or another.

Jessica Black:

I think we’ve all done that.

Becky Thomas:

Yeah.

Ben Forstag:

I think the interesting thing too is, employers end up hiring using the pendulum effect too.

Jessica Black:

Oh yeah.

Mac Prichard:

How do you see that happening?

Ben Forstag:

Well I think a lot of the time, if they’ve been burned by the last employee who had that job, that’s what they’re most concerned about, avoiding that situation again. Even if that’s not core to the job or anything else like that. For everyone, if you get burned, you just want to do the complete opposite. It’s human nature.

Jessica Black:

Yeah, I was just going to say, I think it’s inherent in humans so, yeah, that’s really interesting.

Well I liked what she was saying about, the pendulum definitely resonated with me, but what she said about, your passion isn’t the only thing that you should follow. And that’s something that…I don’t know, people say as just a beautiful sentiment that is not helpful at all. I remember when I was trying to ask folks for feedback of what…when I was trying to figure out my own path, asking people and they were like, “Just do what makes you happy.” And that doesn’t help at all. And what she was saying was that, that doesn’t make the money follow. Following your passion doesn’t automatically mean that there’s going to be money there and I like what she said about making sure that your passion is of service. So obviously, do things that you enjoy. But that’s not the only thing, and make sure that it’s sustainable and that is does match your strengths as well. That it is giving back to the world and it is of being of service for others. I don’t know, I think I may be related to the pendulum effect of, I heard that for so long, and so now I hate that piece of advice of, ‘do what you’re passionate about.’

Mac Prichard:

It’s an important part, but it’s not the only part of figuring out what you should do next.

Jessica Black:

Well yeah, I think that,  that’s not the way to find out what to do.

Mac Prichard:

Right.

Jessica Black:

Definitely use that as a guiding post of, find out what makes you happy, but there are a lot of other things that go into that. So.

Mac Prichard:

She had some very detailed tips about the steps you should go through to figure out what you want to do next. I liked that too.

Jessica Black:

Yeah, I liked that too. Yeah.

Becky Thomas:

Yeah, it should be like a holistic approach. You can’t just be, “This is the one thing, I’m going to go full bore after this”, without really thinking it through and understanding yourself. I also liked what she said about understanding your core challenges. If you were really stressed out at your last job and you don’t address that boundary issue it’s going to follow you. It’s going to continue.

Jessica Black:

Oh yeah, I liked that a lot.

Becky Thomas:

That dream job isn’t going to magically make you a different person.

Jessica Black:

You have to do the hard work. Yeah. I loved that.

Becky Thomas:

Yeah. And I think that’s really important if you’re considering a career change. It’s like you’re imagining this career but you’re still you, in that job, and how’s that going to look?

Jessica Black:

And the entrepreneurial side of things of, just because you don’t want to work in a corporate environment doesn’t mean you can start a business.

Becky Thomas:

Yeah, like starting a business is so easy, right?

Jessica Black:

Right. And that might not be the right fit for you. Maybe the corporate world isn’t but that doesn’t make it the automatic next step.

Mac Prichard:

I loved her point about timing. Because when I see people who have made successful career changes or moved to new sectors, and I certainly experienced this myself, it doesn’t happen overnight. It can take months, or even several years. When I wanted to move from Boston to Oregon it took me about eight months of conversations, interviews.

Jessica Black:

Yeah, it always takes a lot longer than you expect and plan. Yeah.

Mac Prichard:

Yeah, and in the 1990’s I was just determined to get a job in the office of the governor of Oregon, and it took me about three years. But I wasn’t looking that whole time, I just never lost sight of that goal. I always had a day job, but I thought about, “What can I do to move this interest along?” So when an opportunity presented itself I was well positioned. But it takes time, and we have to manage for that.

Jessica Black:

Yeah, absolutely.

Mac Prichard:

Yeah. Well thank you all, and thank you, Kathy, for joining us this week. That was a terrific conversation.

Thank you, our listeners, for downloading this week’s episode of Find Your Dream Job. If you like what you hear, please sign-up for our free weekly newsletter. In every issue, we give you the key points of that week’s show. We also include links to all the resources mentioned and you get a transcript of the full episode as well.

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Join us next Wednesday when our special guest will be Jenn Swanson, host of the Communications Diva podcast. She’ll talk to us about why you’re not getting a job interview after you send in a resume.

Until next time, thanks for letting us help you find your dream job!

Do you fantasize about changing careers? On this episode of Find Your Dream Job, we find out what it takes to completely change your career path, and why so many people want to give up on corporate life and open a bed and breakfast.

Our guest, Kathy Caprino, shares a roadmap for finding the right direction for your career.

Kathy takes a holistic approach to career change, encouraging people to understand themselves and their motivations, and to be patient. She shared 5 steps to a successful career change:

  1. Step back. Refocus on yourself, look at who you’ve been over the course of your life.
  2. Let go of thinking patterns and behaviors that keep you stuck. These cause you to self-sabotage.
  3. Say yes to your compelling vision. If there’s something you’ve always dreamed of doing, decide to take it seriously.
  4. Try it on. Try out your dream, talk to people who have done it, and get past the fantasy.
  5. Create it smart. This process takes time. Don’t rush. Have a plan, then hold yourself accountable.

This Week’s Guest

Kathy Caprino is a career and personal success coach, writer, speaker and leadership developer dedicated to the advancement of women worldwide.

She is the author of Breakdown, Breakthrough, and the founder of Ellia Communications, Inc., and the Amazing Career Project.  Kathy is also a contributor to Forbes, Huffington Post and LinkedIn.

Resources from this Episode